Chestertown, MD Homes for Sale

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  /2

  $59,000

  • Land
  • 1.37 Acres
  • $43,066 per Acre

  0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

  (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

  Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
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  /22

  $1,099,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,784 Sq Ft

  25 Landing Ln, Chestertown, MD 21620

  **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

  Julia Hilfiker Gunther-McClary Real Estate

  25 Landing Ln, Chestertown, MD 21620
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  /53

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  8620 Park Dr, Chestertown, MD 21620

  Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

  Doug Ashley Doug Ashley Realtors, LLC

  8620 Park Dr, Chestertown, MD 21620
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  /23

  $849,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  104 Little Harbor Way, Chestertown, MD 21620

  **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

  Julia Hilfiker Gunther-McClary Real Estate

  104 Little Harbor Way, Chestertown, MD 21620
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  /24

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  7521 Pine Ave, Chestertown, MD 21620

  Priced to sell! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. Bring your vision for this home to life and add instant equity with cosmetic updates! It has been lovingly maintained with a newer roof and

  Maryn LeClair Chesapeake Real Estate Associates, LLC

  7521 Pine Ave, Chestertown, MD 21620
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  /7

  $89,500

  • Land
  • 3.92 Acres
  • $22,832 per Acre

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

  Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. The rear portion of the property is designated palustrine forested shrub wetlands, though

  Maryn LeClair Chesapeake Real Estate Associates, LLC

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
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  /31

  $344,900

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  109 Wilton Rd, Chestertown, MD 21620

  Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large

  Amy Larrauri Chesapeake Real Estate Associates, LLC

  109 Wilton Rd, Chestertown, MD 21620
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  /2

  $38,000

  • Land
  • 0.34 Acre
  • $111,765 per Acre

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

  Dee Dee Miller Long & Foster Real Estate, Inc.

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
• 

  

  /22

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft

  121 Primrose Rd, Chestertown, MD 21620

  Motivated Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright

  William Sutton Coldwell Banker Chesapeake Real Estate Company

  121 Primrose Rd, Chestertown, MD 21620

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